


15 Fic Wincest Challange

by Baconatore (orphan_account)



Series: WINcest Drabbles and Fics [1]
Category: Supernatural
Genre: 69 (Sex Position), Alpha/Beta/Omega Dynamics, Anal Fingering, Biting, Bottom Dean, Bottom Sam, Doggy Style, Dom/sub Play, Drabble Collection, Drabbles, First Time, M/M, Masturbation, Motels, Multiple Sex Positions, No Spoilers, PWP, Passion, Plot What Plot/Porn Without Plot, Porn with Feelings, Public Sex, Rimming, Rough Sex, Sibling Incest, Skype, Skype Sex, Suit Porn, Top Dean, Top Sam, Wincest - Freeform
Language: English
Status: In-Progress
Published: 2015-06-22
Updated: 2015-08-14
Packaged: 2018-04-05 13:11:13
Rating: Mature
Warnings: Underage
Chapters: 9
Words: 3,101
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/4181028
Author URL: https://archiveofourown.org/users/orphan_account/pseuds/Baconatore
Summary: <blockquote class="userstuff">
              <p>1.Cuddles (naked)<br/>2.Kiss (naked)<br/>3.First time<br/>4.Masturbation<br/>5.Blow job<br/>6.Clothed getting off<br/>7.Dressed/naked (half dressed)<br/>8.Suits (Was Skype Sex but i changed it <3)<br/>9.Against the wall<br/>10.Doggy style<br/>11.Dom/sub<br/>12.Fingering<br/>13.Rimming<br/>14.69<br/>15.Sweet and passionate<br/></p>
            </blockquote>





	1. Naked Cuddles

**Summary for the Chapter:**

> Naked Cuddles starring Sam and Dean! (Dean being cuddly and Sam being a lil bitch)

Authors Note: Going to try and put one chapter a day until completed; if I don't its because 1, im on vacation 2, busy, or 3, lazy :3 So please be patient with me. Also, no spoilers for any seasons. This is basically PWP :) Anyway, Thank you <3

 

 Chapter One: Naked Cuddles

 

 "Dean, its literally almost one hundred degrees in here."

 "So?"

 "It's too hot for this."

 "I don't care."

 "Seriously, You're sticking to me."

 Dean said nothing but shut his eyes and curl into his brothers back. Sure, it was hot, that's why they were naked in the first place; but Dean _needed_ to be cuddled and if Sam wouldn't do it for him, he'll do it himself.

 "Dean."

 He was quiet.

 Sam sighed to himself and rolled over, putting his arms around Dean's neck and bringing him back. He watched as his brother's frown turned into a smile as he placed his head on Sam's chest, cuddling up to him.

 So much for the hot weather.


	2. Naked Kisses

**Summary for the Chapter:**

> Naked Kisses featuring Flushed Sam and a rlly dominate Dean! (Im trying to make these chapters longer shhhhh)

Authors Note: Aren't they adorable? <3 (By the way, i'm leaving EXPLICIT sexual content for when it gets really...you know....explicit. For now its just mild stuff <3

 

_**Naked Kisses** _

 

 Dean grinned and kissed Sam's lips once again. His little brother was still damp from the shower that he had taken prior and therefore, his hair fell into his face. Sam flushed and put an arm around Dean's back, holding onto him slightly.

 "We should get dressed," Sam said almost in a whisper.

 "Why? I'd just have to undress you again."

 His face was red. Dean loved to tease.

 He smirked again and started to trail his fingers down Sam's back, kissing his lips lightly but enough to drive him crazy. He put a hand through Dean's hair, gripping and pulling it because, from experience, he knew that Dean really did like that kind of stuff, and it sure as hell got him going. He growled under his breath, biting Sam's bottom lip in the process. Their naked bodies were pushed together, leaving no space between them while they kissed, and Dean continued to trail his fingers over Sam's behind.

 "I- oh. Am I interrupting something?"

 Dean turned around and grabbed the sheet from the bed, covering him and Sam.

 "Christ Cass- you could have called."

 XXX


	3. Sam's first time

**Summary for the Chapter:**

> featuring a soft Dean and a flushed Sam, once again! aaaaaaa  
> (I prefer Dean on the bottom but you know ill make an exception for this one)
> 
> also these will get longer I promise. I plan to make them around 600 words each at LEAST. im just busy (doing nothing) with other things and cant just sit around and write gay porn while my parents are looking over my shoulder :D I wrote a shit ton of smut/yaoi/yuri on my other account so I guess if that's what you're looking for, look there until I write more here haha.

Authors Note: This is kinda explicit don't say I didn't warn you :D

 

  ** _Sam's First Time_**

 

 John had a job; he was hunting a pack of demons and left Dean to take care of Sam for a day or two at the motel that they had been staying at lately; it was only around fifty dollars or so a night, so it was a steal for John Winchester.

 "De?"

 "Yeah?"

 Sam didn't answer, but stood at the foot of the motel bed. Dean glanced up from the gun that he was cleaning and looked at his brother, face red and looking away from his big brother's glare.

 "Sammy? What's wrong?"

  Dean glanced down at his pants; he saw that there was a small tent forming in his pants.

 "Oh."

 "Dean- I- I want to..."

 Dean put the gun on the table and got up. "If you wanted me to take care of that for you, you should have just said so." Sam slapped Dean's hands away with a frown. "Actually, I wanted to do something different this time."

 "Oh. Alright. What is it?"

 "I want you to do me."

 Dean's eyes widened a bit. "What?"

 "You know what."

 "Sammy, damn it- I should be teaching you to protect yourself, _not_ to take a dick in the ass. I was okay with helping you out but don't you think that-"

 "Its my body, isn't it? I can decide what's best for me."

 "I know Sam, but im your big brother. I don't want to hurt you."

 He smiled a bit and took a step towards Dean. "I know. I know you don't, so you wont hurt me. I promise. Please?"

 

 Dean couldn't argue with Sam's puppy dog eyes.

 

 "De, f-fuck, please-" Sam hissed, his hips thrusting backwards on Deans fingers. Dean wanted to just fuck him already, he did, but he wouldn't risk hurting Sam like that. He had to stretch him out because it was pretty obvious that he had never done it with a guy before. Hell, Dean was almost positive that his brother hadn't ever done it at all- he usually never left Dean's side. And of course, he didn't want to toot his own horn or anything but he wasn't exactly small. Dean wasn't sure how the hell Sam was going to take him. Dean slid the condom onto his cock and adjusted it so it was on comfortably. He glanced down at Sam beneath him, whimpering and moaning and wanting; and _damn_ , it got him all worked up.

 "Are you ready Sammy?"

 "Yes! Yes, please, De~"

 Dean aligned the tip of his cock with Sam's arse; with a small push, the head was inside and Sam let out a moan that was so amazing Dean was sure his ears would melt.

 He slowly started to thrust in and out at a slow pace, Sam gripping onto the sheets of the Motel bed beneath them. He began to thrust his hips down on Dean, so Dean began to pick up the pace, still being careful not to put in too much and hurt him. He held to Sam's hips, holding so tightly that he would probably bruise them; but Sam didn't seam to care, he was in his own little world in that moment. His eyes were closed and his body bounced to the rhythm of Dean's thrusts, and the moans that escaped Sam's mouth were blissful for the elder.

 "Dean- fuck- im gonna come-"

 Dean took Sam's cock into his hand, thrusting harder than before, a grunt escaping his lips. It only took a few more to have them both over the edge, Sam coming on his chest and Dean into the condom. In a pile of moans, it was over, and De collapsed next to Sam on the red blanketed bed.

 XXX


	4. Masturbation, feat. Dean

**Summary for the Chapter:**

> Dean has fantasies.

Authors Note: I love the idea of Sam topping Dean so hard like come on. Even though he's the little brother, he's bigger than Dean and could pretty easily top him  (¬‿¬)… So yeah. Here's chapter four I think!

 

_**Masturbation, feat. Dean**_

 

 Dean had weird fantasies.

 It's not his fault, after all. He couldn't control how his mind acted and what it thought of! And even if he could, he would never admit the fact that he didn't want the fantasizing to stop. He liked it in some aspects.

 But fantasizing was one thing. Maybe he could forget if he was thinking about Sam. He could push that down and maybe it wouldn't have been so weird for the elder, but there was something off about the things he thought about.

 Sam was the one on top.

 He had never really let a girl take control in the bedroom; it was always him. He liked to feel in control, liked to please the other person he was with but for some odd reason, he got off to thinking that Sam could over take him.

 He pulled down his pants.

 It started off easy; Sam would take him carefully by the hip and pull him in close, placing little kisses on Dean's lips and neck area. Dean, in turn would allow this and wrap his arms around the taller mans neck, running his hand through Sam's soft hair. Sam would then trail one hand down his back, running his hands all over Deans bottom and slowly slipping his hands into his pants.

 But no, it would change from there.

 Dean would think about Sam tying him up, strapping his hands together with rope and making Dean suck him off. He thought about Sam face fucking him to no end, until he couldn't take anymore of it. He wanted Sam to then pin him on the bed and fuck him fast, hard enough to make Dean moan and scream. He imagined Sam teasing him, jerking him off but not letting him come unless Dean begged for it. Things that he had never done, or even thought about doing with someone before would run to his mind and wonder where the hell he had read something like this; but he didn't. His mind just couldn't help but think about these things, and Dean couldn't help but to get off to it.

 With these thoughts in mind, Dean came onto his shirt.

 

 

 "Dean? You in there?"

 "Fuck." He whispered. "Yeah, im in here!"

 Dean whipped off his shirt with a towel and sighed. He unlocked the door and stepped out.

 "Why were you in there so long?" Sam asked.

 "Oh, man, you know. Just doing things."

 Sam shot Dean a glance and Dean avoided it.

 "Yeah. _Things_."

 

 

XXX


	5. Blowjobs

**Summary for the Chapter:**

> Featuring a cute moany dean and a cutie patootie sammy

Authors Note: So, again, sorry for the length. Writing is hard :( Well, not really for me since ive been doing it so long but I guess I just don't have any, like... _want_ to do so anymore? Don't get me wrong, writing fanfictions and other stuff is definitely a passion of mine but I guess Im just too tired all to do it most of the time. :p

~~"JUST DO IT"- Shia LaBeouf~~

 

_**Blowjobs** _

 

"F-fuck, faster Sammy."

Sam grinned and started to go back and fourth, his hands cupping Dean's balls at the base.

They were in another motel room, like always. This one was slightly darker and damper than the others that they had been in, but somehow they always made the best of it. Sam sat in-between Dean's legs, his lips curled around his hardened cock. Usually, it would be Dean giving Sam the blowjob but he insisted that he did it this time.

Dean thrust forward slightly into his mouth, almost involuntary. It had been a week or two since he had gotten off due to the newest case which was harder than he originally thought it was going to be, but with the demons finally dead and the town saved for the moment, they finally had a moment to themselves.

 "Sam, shit, im gonna-"

 Dean could practically see Sam grinning down there, enjoying his brothers moans and pleads. Of course, Dean would never usually moan or plead but he made exceptions sometimes- because apparently Sam liked to _think_ that he could be top.

 Yeah, yeah...its not like Dean was actually enjoying this...

 Sam deep throated him and allowed Dean to come into his mouth; in which Dean would joke about later. However, in the moment, Sam looked up and saw that his brother's face was pure bliss; like someone who had gotten a million dollars. His hands were entangled in Sam's hair, pulling ever so slightly but not enough to hurt.

 Sam liked Dean like that; so submitting.

 He stood up and wiped his mouth. Dean slowly zipped up his pants and watched as Sam shot him a glare of victory, and Dean decided to growl and look away.

 "Shut up."

 

XXX


	6. Clothed Getting Off

**Summary for the Chapter:**

> Featuring a sleeping dean and a horny sam!

Authors Note: Inspired some TWD fanfiction I saw a few years ago. :3 Thanks for all the kudos too, guys, I really appreciate it!

 

**Clothed Getting Off**

 

 Sam made another small thrust into his brother's leg with a whimper.

 Dean was asleep. His eyes fluttered, probably in some dream with sexy girls and lingerie, his body curled up into the blankets of the king sized motel bed. The clerk had looked at them awkwardly when they had asked for a single bed, but they managed to get one all the way down the hall where nobody would hear them if they had sex.

 But Sam didn't want to wake him up. Dean hadn't slept a lot in the past few days, and it was almost three am, so he decided he might as well take care of his problem on his own.

 His pants were tented up as his boner was pretty obvious, he had woken up to it about ten minutes ago; he couldn't remember what dream had caused this, but Sam was pretty sure that it had to do with Dean.

 So he grinded up to Deans leg, and slowly and softly thrust forward.

 He bit his lip and continued to do so, making small noises but still managing to keep his cool. He just wanted to get off, and go back to sleep and pretend like it never happened.

 Sam couldn't help but, when he felt the familiar tightening in his gut, thrust harder on Deans leg; and with a few fast harsh thrusts, he came with a grunt into his pants.

 With a sigh, he sat back into the bed and closed his eyes; he could take care of the wet spot in his boxers when they woke up. He didn't have the energy to even think about getting up to clean it.

 As he closed his eyes, he felt a pair of cold arms wrap around his neck and snuggle into his chest.

 "Night Sammy."

 

XXX


	7. Dressed/naked (half dressed)

**Summary for the Chapter:**

> Needy Sam :3

_Authors Note: I'm not doing Skype sex for the next chapter. Ill have to find something else to do bc im not doing that ;p Its mostly because i just don't think that Sam and Dean would do that, let alone ive never written something like that before (because cybersex is_ way _too overrated.) Anyway, enjoy the chapter and please leave suggestions on what you would like to see in the future! Im thinking about writing some Destiel....._

 

**_Dressed/naked (half dressed)_ **

 

 Sam lifted himself up and down onto Dean's lap, the small whimpers that he made sending shivers down Deans spine. Their shirts stuck to their bodies, because they had been so horny and rushed that they didn't care that they had left them on. Besides, Dean liked when his shirt smelled like Sam. It was pleasant.

 He held on tightly to Sam's hips,  kissing his neck as he did so to try and comfort his little brother. Sam, however, could handle it, and was able to take Dean's entire length into himself- and despite what he would have thought, this was better than any girl Dean could have picked up at a bar or something. Maybe it was the fact that they loved each other, in more than one emotional way, or the fact that they were so dangerously codependent on each other. But whatever it was, he was more than happy to be looking up at Sam's face full of pleasure than some hooker.

 "De, ah-" Sam would moan into Deans ear, with the voice of an angel he proposed. The sounds he made were bliss for the older, and Dean would kill a million demons to hear him like that all the time.

 "Sammy, you're so tight," Dean remarked, brushing the hair from Sam's eyes. He saw Sam's face light up red, and he would look away from Dean. Sam was a shy one in bed, sometimes more than others, and it just made him all the more cute.

 Adorable, absolutely adorable.

 "Dean, please, fuck- im gonna come," Sam moaned, his hands gripping Deans hair.

 And of course, Dean obliged- he started to thrust harder into Sam, making his thrusts faster each time.

 He watched as Sam came onto Dean's Kansas shirt, the white spurts of come visible on it. With a few more thrusts, and a grunt, Dean came into Sam.

 

 "Gross, you came on my shirt," Dean remarked a while later, both of them now fully clothed.

 "You came inside me, you dick."

 Sam placed a small kiss on Deans forehead.

 

 XXX


	8. Suits.

Authors Note: Like the phone sex kink? Im going to do that instead of 'shy' on chapter...something. Anyway, i love suits and decided that this would be hawwwt <3 (Did i really just say 'hawt'.)

 

 Suits.

 

 Dean really liked Sam when he wore that suit.

 Sam in a suit was the most blissful thing that Dean could ever see; he looked so professional, which was the point, but it made Dean hot. He couldn't help but stare when Sam was getting changed into it to go on a case; its not his fault, though, it was Sam's for being so damn attractive.

 "So, demons at a church; wonder how they can stand it there."

 "Mhm."

 "I wonder how they got around praying, or touching the holy water. I mean, why would they want a bunch of priests dead?"

 "Yup."

 "Dean i would appreciate it if you stopped staring at me."

 Dean looked up to meet Sam's gaze. "What? Im not staring at you."

 "Yeah, you were," He chuckled and eyed Dean up. "You okay, De?"

 His face turned red as he sat back in his chair. "Its not my fault you look fuckable in those suits."

 Sam grinned. "What was that?"

 Dean looked away, realizing that he just said that out loud. 'Im already deep in shit,' he said to himself, standing up and taking Sam's tie tightly.

 "Fuck me, right now," Dean growled.

 Sam chuckled and pinned Dean to the bed behind him. "Someone's needy," He remarked, kissing his lips harshly.

 "Yeah yeah, whatever. Just fuck me."

 

XXX


	9. Against The Wall

Author's Note: I am SO sorry for the lack of updates. We're on hiatus now because i have some shit on my other account (TWDnSlenderverseFangirl, Shameless self promo) to deal with. Plus school. So, here you go! :)

 

 Occasionally, Dean's back, mostly spine, would be covered in bruises. Because sometimes, shit happened and stuff got heated, and occassionaly he was against the wall. Most of the time they were easy to ignore, but hiding them from Sam was always a challenge.

 "Dean?" Sam asked, tilting his head at his older brother.

 "Yeah?"

 He hesitated for a moment. "Why are you sitting like that?"

 "Like what?"

 " _That_." Sam replied with a faint smile. "You look like a kid playing with dolls."

 Dean was on his stomach on the motel bed, legs dangling in the air, reloading all the guns that were scattered on the bed.

 "I do not."

 Sam rolled his eyes. "Okay, then just sit up normally."

 "Uh...no."

 He walked over to Dean and looked at him cautiously. "....why?"

 With a glance, he pulled up his pale blue shirt to show his back.

 Sam almost couldnt stifle his laughter.

 "What?!"

 "Dude...we're never doing it against the wall again," He said, running his hands gently over the bruises and marks.

 "Yeah, well maybe if you calmed the hell down sometimes."

 "You werent complaining when it was happening."

 

 ....Touche.


End file.
